


A Pain in My Ass

by Cimorene105



Series: Rodeo [7]
Category: Supernatural
Genre: Aftercare, Alternate Universe, Anal Fingering, Anal Sex, Angst, BDSM, Bad Puns, Bottom Castiel (Supernatural), Bottom Castiel/Top Dean Winchester, Boys In Love, Boys Kissing, Candles, Castiel deserves nice things, Cowboy Castiel, Dean Winchester Is A Good Boyfriend, Dilator use, Dirty Talk, Dom Castiel/Sub Dean Winchester, Emotional Hurt/Comfort, Fluff and Smut, Good Significant Other Dean Winchester, Hurt/Comfort, Like a lot of prep, Lotsa prep, M/M, Making Love, Marking, Mechanic Dean Winchester, Openly Bisexual Dean Winchester, Pet Names, Praise Kink, Romance, Safe Sane and Consensual, Schmoop, Servicing kink, Sex Toys, Slut Dean Winchester, Top Dean Winchester, and they deserve it, dean baking, everyone is different guys, openly nerdy Dean Winchester, some people need more prep
Language: English
Status: Completed
Published: 2019-10-24
Updated: 2019-10-24
Packaged: 2021-01-02 11:02:03
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 3,593
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/21160589
Author URL: https://archiveofourown.org/users/Cimorene105/pseuds/Cimorene105
Summary: Cas wants to trust Dean with the process of making love to him - and it is definitely a process. From his point of view, he's damn lucky to have such a patient partner. Dean just wants to give him nice things.





	A Pain in My Ass

**Author's Note:**

> YOOOOOOOOOO - guess who's back, back again.
> 
> My muse took its sweet time finishing this thing. I missed you all!
> 
> This series kept me sane in uni, and I'm so grateful for every comment and bookmark you all leave me. Thank you for reading!

Dean yelped. He'd no doubt burned himself because he'd forgotten an oven mitt again.   
  
"Don't hurt yourself," Cas sarcastically but casually called out.   
  
"Yes, Sir," Dean sarcastically and more irritably tossed back.   
  
Cas realized he'd been a bit harsh. He got up and crossed to where Dean was now holding his hand under running water. "Perhaps I didn't make myself clear," Cas rumbled, his fingers threading gently through, then lovingly tightening in Dean's hair. "What I meant to say was, 'Don't. Hurt. Yourself.'"   
  
Dean's breath caught. "Yes, Sir. Sorry, Sir," he whispered back.   
  
"Thank you for agreeing to be more careful, Dean. I have oven mits for a reason." His fingers loosened slightly, and he nuzzled his face in Dean's neck. "And I'm sorry I snapped at you. I worry, but that's no excuse."   
  
Dean sighed. "I know you didn't mean it like that, but thanks. I just forgot about the stupid freaking mit."   
  
"I know, which is why I try to remind you. I'm sorry I didn't catch you in time."   
  
Dean sighed again. "It was my own damn fault. I'm thirty-two. You'd think by now that I'm old enough to remember on my own to use one."   
  
Castiel kissed his neck, which gave him an idea. Dean felt the smile grow. "Let me kiss it better," Castiel seductively growled.   
  
Dean shuddered at the tone. He lifted his hand from under the cold tap. Castiel kept his head down where he was leaning on Dean's neck, but guided Dean's fingers up to his face. He sucked them all into his mouth.   
  
Dean grinned at him, then let himself be affected by the warm, wet, gentle suction. "God, your mouth, Cas. It still hurts, obviously, but I'm guessing your plan is to distract my brain from it. Good idea."   
  
Castiel let Dean's fingers fall from his mouth and said, "You weren't very in control of the situation. Would you like to feel like you've regained some control?"   
  
Dean turned to quirk an eyebrow at him.   
  
Cas grinned fondly. "I've been wanting you to make love to me for a while."   
  
Dean stopped breathing. "I've been wanting to make love to you for a while."   
  
Castiel's smile became smaller and softer. "Is now a good time?"   
  
"Well, I did just bake pizza and cookies."   
  
Cas made a face. "At the same time?"   
  
Dean shrugged. "Yeah. Why not?"   
  
Castiel chuckled and shook his head. "Let's eat some now and some after."   
  
Dean grinned. "Good plan, Sir."   
  
They ate half of the pizza together and a cookie each, Cas stopping Dean from grabbing more of both. "Have a pear."   
  
Dean pouted, hoping to sway Cas with his cute face.   
  
Cas shook his head.   
  
Dean ate a pear.   
  
"Since we've just eaten," Cas shared his thoughts while also snatching up a pear, "it'll be a while before our bodies are ready. Let's ice that burn and then you can show me how to do an enema."   
  
"You've never had one before?" Dean asked between bites of fruit.   
  
"I have. I just don't want to do it by myself," Cas replied between his own bites. He figured he was allowed to sometimes ask for help and company.    
  
"I get that. It's a weird feeling, isn't it? Mostly I just get impatient," Dean commented. "I heard there's this great shower attachment that works a lot better than pharmacy kits, but I tend to use my money on other things," Dean informed him.   
  
Cas hummed in consideration. "I might look into that."   
  
Dean acknowledged the decision with a nod. "Cool."   
  
They watched a movie together while Dean iced his hand, then headed to the bathroom. Getting an enema was indeed an interesting sensation that Cas usually didn't bother with. He'd had a niggling thought it would be more humiliating with a partner, but Dean treated it like a routine, mundane exercise and heaped Cas with praise on how well he was doing.   
  
Dean was right, Cas thought. The most annoying part of the process was always how long it took. Dean anticipated his overeager Dom would start losing his very considerable patience soon, so Dean did a dramatic reading of Captain America comics to entertain them both.   
  
Soon enough that they were startled out of their laughter, the timer went off and it was time for the rest of Cas's prep. They used Cas's enema kit a second time and started the process over.   
  
What Dean was really looking forward to was fingering Cas. He didn't do it that often because he was usually so preoccupied with bottoming himself. It was always a special, intimate occasion when they switched.    
  
Dean soaped up his hand and regretted that Cas had to face away from him for now.   
  
"It's fine, Dean. This won't be the last time by any stretch. " Cas winked to get his pun across. Dean was, in fact, stretching him.    
  
Dean rolled his eyes and laughed, shaking his head at his boyfriend's antics. He kissed Cas's butt cheek and deemed his boyfriend clean with a last swipe around Cas's rectum. He rinsed off the soap as best he could, trying to somewhat rein in his enthusiasm - Dean was always excited when he really got to stretch Cas out.    
  
“Wait here,” Dean requested. He disappeared into the bedroom for a minute. Castiel heard rustling and at one point a  _ clank - “Ow, fuck!”  _ before a hand beckoned him through the crack in the doorway.   
  
Castiel opened the door and felt his body heat with love and appreciation from his toes to his grinning cheeks. Low light flickered against the walls from every surface. Dean had lit a forest of candles for him.   
  
“You remembered,” Cas remarked fondly. It was clear Dean had gone to a lot of trouble to find his candles and possibly purchase a few more sets besides.   
  
Dean moved to hug him from behind. “Of course,” he replied. “Gotta romance my boyfriend and show how much I appreciate him.”   
  
Castiel looked over his shoulder to meet Dean's eyes. From such close proximity, Cas could almost count the freckles on Dean's nose, if he fought not to go cross-eyed. He pressed a kiss to the freckled skin, then dipped in for a full kiss on the mouth. Dean hummed back to Cas in satisfaction and tugged at his arms to turn Cas fully towards him.   
  
Dean moved them to the bed and snatched up the lube. He loved the feeling of his skin against Cas's, no matter the situation. Dean slid up the bed, kissing his cowboy's toned muscles as he went. Just to be a little shit, Dean made eye contact and gave a short, tantalizing lick to the head of Cas's cock, then moved on right away.    
  
Cas chuckled weakly.   
  
Dean grinned in triumph. As his fingers found their way back into Cas's ass, he latched onto a dark nipple. Dean slowly and resolutely dragged the two fingers apart, watching as Cas relaxed into it, loving the way he groaned with the feeling.   
  
Cas blearily opened his eyes. "Why do you always spoil me when we do something like this?"    
  
Dean smiled adoringly up at him. "Just repaying the favor, Sir."   
  
Cas chuckled again. "And you do it so well."   
  
To prove him right, Dean searched out Cas's prostate and gave it a few caresses. He kissed Cas's sternum to be closer to the sound of his long, low moan.    
  
When Cas felt like he was floating, Dean slowly began working in a third finger. This was always a little uncomfortable for Cas, as he didn't do anal play on himself very often. They always had to go so slow at this point that he wondered briefly every time if this wasn't a good idea; if he just wasn't built to take much more than a good fingering. Everyone was different - maybe this was just something he couldn't do.    
  
Cas didn't realize he'd been mumbling his thoughts until Dean laid his clean hand on Cas's face and said, "Babe. Babe, look at me."   
  
Cas looked. The gaze he met was a familiar one of concern and reassurance.   
  
"You're forgetting that a lot of your experience comes from me, and I am a needy bottom." Cas laughed at the earnest tone and the accuracy.    
  
Dean continued, "What kind of lover would I be if I couldn't be patient enough to give you the prep time your body needs?"    
  
He had a point, there.    
  
"Yeah, everyone's unique, and your particular quirks are not bad, Cas. If you don't want to bottom, that's different." Dean raised his eyebrows. He knew his Dom sometimes forgot he was allowed to have boundaries, too. "We don't have to if you don't want to. But I'm more than willing and patient enough to take as long as you need, every time you want to do this."   
  
Cas nodded. He wanted to. He just didn't bottom very often because it took longer than he usually wanted to wait. That time Cas had tied Dean up and rode him, Cas had slowly prepped himself for over an hour to make sure he was ready - and not many people were willing to take that long. Cas knew Dean always came through for him, but he still needed this reassurance. "I do want to. Thank you, Dean. It’s just that I know this is always a pain in my ass."   
  
Dean laughed, then scooted up to kiss him, breathing, "Of course, Cas," into his lips. He drew back again to ask, "Shall I continue?"   
  
Cas nodded and surged up to take Dean's lips again. Dean chuckled into Cas's mouth. They could switch up the roles, but they couldn't take the Dom out of Cas.   
  
"Come on, babe, let me do this for you," Dean implored, crooking his fingers and making Cas moan.   
  
"If you insist." Cas smirked at him.    
  
"I don't insist," Dean corrected him. "You just want me to; isn't that right, babe?" Dean pecked a kiss to his cheek.   
  
Cas gave a breathless, "Yes," and then Dean was kissing him, fondling his dick, and fingering his ass. Cas lost track of time while Dean took him slowly and sweetly, devoting his energy to making Cas feel loved. It was one of those moments when Cas was aware time was passing, but it both felt like the time had stopped and sped up.    
  
If every second was a new kiss, Dean was making time stop and start with his slow, sensuous mouth. His patient, persistent fingers were an added bonus. Dean paused occasionally to add more lube, and this gave Cas the opportunity to appreciate his amazing lover. At times like this, with Dean hovering over him, focusing so intently on him, Cas felt like he was being rewarded with the chance to feel how he so often made Dean feel.    
  
Cas could feel the tangible love and care radiating from his partner - in Dean's lips, in the fingers slowly stretching him, in the hand that roamed his erogenous zones, and especially in the way Dean looked at him. It was the sporadic encouragement, however, that never failed to bring tears to Cas's eyes when Dean was in charge.   
  
"You're doing so well, babe," Dean whispered. "I love kissing you; I'll never get bored of this - any of this. I could spend all day fingering you. That what you want, babe?"   
  
Cas nodded. Dean grinned. His fingers would get tired, so before that could happen, he switched over to Cas's set of dilators. It felt like a short eternity had passed before Cas was finally taking the largest dilator comfortably.   
  
"I think you're ready, babe. You ready? What do you think?" Dean gave a movement with his hand to imitate the way he would fill Cas with his dick, so Cas could say whether he felt ready for it.   
  
Cas's breath caught and then he moaned when he realized what Dean intended with that movement. "As usual, you blow my mind with your patience, Dean. I'm - I'm ready."   
  
Dean mistook Cas's pause for hesitance. "Hey," he got Cas's attention, "I can go longer. My arms might give out at some point, but I can switch over to a vibrator and just do this for hours if you want. And so you know," Dean confessed, "it's got nothing to do with patience. I love this. I love making this all about you. You don't do very many nice things for yourself, so I'm more than happy to treat you like you deserve." He gave Cas a pointed look.   
  
Cas grinned wryly. Dean was right; he didn't do enough nice things for himself. "Thank you, Dean. I am ready, though."   
  
"You're sure - you're not just saying that?"   
  
Cas nodded. "I'm positive."   
  
Dean nodded back at him and let the dilator slide out of his lover's ass. He took a second to slick up his cock and then he was sliding back into Cas's rectum. Dean shuddered as he slowly filled the space he'd made for himself. When he was fully seated, he leaned down on his elbows so he could touch Cas's face and quietly ask, "How you doing, babe?"   
  
Cas breathed heavily and tried to focus on relaxing his ass. He reached down to stroke his dick and keep the moment pleasurable for himself. Castiel tried to nod so Dean wouldn't think something was wrong, but he needed a minute or twenty. "Adjust" was too lax a word for the intensity and fullness, for the stretch that could become too painful too quickly if they weren't careful. Cas was thankful that they'd tried more mild versions of this before, because Dean knew how to help.    
  
“You want me to dirty talk you, babe?” Dean nosed at Cas's jaw, rumbling low.    
  
Cas's body gave an involuntary shudder and his muscles clenched, prompting Dean to groan in his ear at the pressure. “God, yes,” Castiel breathed.   
  
Dean chuckled warmly. He held himself up on one elbow so he could drag his other hand down Cas's neck, over his chest, and across his hitching abs. “Fuck, Cas - you're so goddamn amazing. Can't believe I get to have this with you.” Dean laughed again, like he was sharing a secret with his boyfriend. He nuzzled their noses together. “Thank you for inviting me into your body, where you rarely let anyone play. You must trust me a whole hell of a lot, Cas - and you have good reason to. I'm gonna make you feel so good; gonna turn you into a shaking, messy puddle.”    
  
Dean was almost growling by the end of his pronouncement. Cas had thrown his head back and was doing his best to fuck himself on Dean while being trapped under the weight of his body. Dean followed suit, throwing his head back and just barely moving his hips to meet Cas's thrusts.    
  
Castiel groaned out Dean's name, sounding wrecked.   
  
“That's it, Cas. Let go; let me give you what you need from me. I got you. Oh, God, Cas. You feel so good.” Dean screwed his eyes shut, focusing all his energy on slowly fucking his partner.   
  
They lay together, barely moving, slowly and gently writhing, moaning their pleasure to each other. Castiel stretched his arms above his head and arched his torso, unconscious that his efforts to get comfortable made for an alluring show.    
  
“God, you're so gorgeous, Cas,” Dean whispered. He leaned down to kiss the stretched neck that was bared to his gaze in the same way Cas left himself emotionally vulnerable to Dean. Castiel brought his hands down to run lightly over Dean's back, causing a shudder that made Cas smirk. He kissed the part of Dean's face that he could reach while Dean panted against Cas's pulse. “That's fighting dirty.” Dean's protest was ruined by his moan when Castiel slid a finger down Dean's ass crack. “And that's really fighting dirty.”   
  
Cas chuckled. “Alright, I'll stop.” He removed his hand from where he'd been teasing Dean's hole. Dean didn't want this to be about his ass right now, which was valid. Thinking about Dean's ass reminded Cas to check in with his own. The fit still felt pretty tight, so they would probably be at this stage for a while. “What would you like to do while we wait?” he asked.   
  
Dean’s expression warmed Castiel to the core. “I could make out with you for hours,” he murmured intimately. “You game?” Dean pressed a peck to Cas's lips.    
  
Cas nodded and rubbed his hands soothingly up and down Dean's back. Whenever Dean kissed him, and then kept kissing him, it felt to Castiel like it would take Dean a monumental effort to stop again. He always would stop if Cas ever asked him to, which was a rare occurrence, and Dean would do so graciously. That didn't stop Dean's yearning for the contact, though, and he was never very good at turning off the “come fuck me and kiss me senseless” vibes. Cas knew he was no better - might, in fact, be worse - but Dean's constant longing always struck him with its intensity.   
  
This time was no exception. Dean kissed him and it felt like worship. Dean kissed him and it felt like love. The absolute focus and dedication Dean gave made Castiel realize all over again how much Dean wanted him. If Dean could talk while kissing Castiel, Cas might classify the words coming from Dean's mouth as prayer.    
  
Dean would be the first to claim that Cas wasn't perfect. He would, however, still be the first to call Cas his angel; his imperfect, quirky, humany angel.   
  
Cas let the tension melt away from his body to make room for the love Dean selflessly gave.   
  
"Cas," Dean eventually murmured, "I love this. I love making love to you." He kissed down Cas's cheek and jaw to his neck, where he sucked a harsh, sloppy mark. Dean ran his hand down Cas's side and gripped the back of Cas's knee, slowly lifting it. "This okay?" he rasped behind Cas's ear.   
  
Cas shuddered at the new closeness and nodded. He clenched and relaxed his ass, feeling Dean move a little easier now. Their combined patience was paying off.    
  
Dean pulled back and smoothly thrust forward again, the new angle inadvertently giving him direct access to Cas's prostate.   
  
The man underneath him gasped and breathed out a moan. His nails cut into Dean's shoulders and his raised leg tightened on Dean's waist. Cas clenched his eyes and a tear slipped down his cheek.   
  
Dean paused, having never before seen this kind of reaction from his boyfriend. It was probably good, but it could also be bad. "What color, babe?"   
  
"Dean, oh god, green, green," Cas whimpered.   
  
Dean grinned and slipped his hand up Cas's tensed thigh towards his straining dick. It took a few minutes for him to coordinate his thrusts and tugs on Cas's cock. He eventually realized the key was to let the movement from his hips push Cas's cock through the tunnel of his fist. Once he figured it out, Cas responded by lifting his other leg to clamp Dean tightly between his thighs and rake his nails down Dean's back. Cas's head tipped back again and a high keen ripped from his throat, almost a sob.    
  
Dean focused on his rhythm and how fucking good Cas looked and sounded underneath him, which didn't leave much brainpower for talking. His eyes fogged over. Dean fought to keep going until he'd made his partner come.   
  
Soon Cas was breathily chanting Dean's name and his whole body was tightening up. "Oh god, Dean, oh god, oh god,  _ fuck, Dean _ \- " and then he was coming, neither of them aware what kind of sounds he making.   
  
_ "Yes, Cas!" _ Dean finally let himself go as well and continued to hold Cas's dick as he slowly thrust through his orgasm. He pried his eyes open to see Cas's flushed and shining face beneath him, panting as hard as he was. "You too sensitive, babe? I can go on a little longer if you want."   
  
Cas hesitated. "Could you just…" He didn't want it to be over, but he didn't want any more stimulation. "Just stay? Still? ... And just hold my dick? Is that weird?" If he wasn't already bright red from the exertion, Cas knew he'd be blushing.   
  
Dean smiled and settled some of his weight on his boyfriend, not loosening his grip on the man's dick. "Of course not. I don't mind that at all." With more of his weight supported, Dean could rest his other hand on Cas's body as well, seeking to be even closer. He placed a gentle kiss on Cas's still panting lips. The breath whooshed over his face and was buffeted back with his own harsh breath.    
  
"Goddamn, I love you, Cas," he breathed.   
  
Cas sighed as his breathing began to slow to normal. "I love you so fucking much, too, Dean. Thank you." He moved his arms to cross over Dean's back and keep him close.   
  
"You are so welcome, Cas. Anytime. I mean it." Dean tucked his face into Cas's neck.   
  
Cas's eyes crinkled, his lips stretched over his gums in a wide, incredulous smile, and he swiped away another tear that crawled slowly down his cheek.  _ I'm the luckiest fucking bastard,  _ he thought to himself. Cas kissed Dean's cheek and reached for his phone to set a five-minute alarm, trusting it to wake him and his lover for their aftercare and all the loving adventures they would have after.


End file.
